As someone approaching his mid-50s, Robert Maurone should be starting to think about winding down his career, not beginning a new one. Of course, if you agree, you don't know Robert, or Bobby, as everyone except the folks at the IRS and DMV know him.

A few years ago, Maurone was a Wall Street corporate type, feet on the floor at 4:15 each morning so he could catch a train from Philadelphia to his Manhattan tech job. In 2010, he started to reconsider his future. "Years ago, my dad shared some borrowed advice," Maurone explains. "He said, 'If you love what you do, Bobby, you'll never work a day in your life. With 100% support from my wife, I decided to become an insurance agent. I studied the business, did research and talked to trusted advisors—people I knew in the business."

Last year, he settled on commercial P&C as his specialty. That felt most natural because he was, as he says, "the guy who signed checks for general liability, commercial auto, workers comp and umbrellas when I worked in my dad's family business. I had a good feeling about P&C products and the protection they offer."

He passed his licensing exam on the first try, interviewed with five Philadelphia-area agencies, and got three offers. Maurone opted for Bridgepoint Insurance Group, where he's now a vice president because, he says, "Bill [Dalton, Bridgepoint principal] understands insurance, he knows where he wants to take the agency, and he walks the walk.

"He already had another mid-life-career-change producer on staff, so I knew it could be a good fit," he adds. "Plus, the younger people on staff are smart and energetic, and their enthusiasm attracted me."

According to Dalton, a number of things worked in Maurone's favor. "His sales acumen, his proven history of developing relationships, and his experience in the business world were all positives," he explains. "We are niche-oriented, and Bobby had knowledge of some segments he wanted to build on. That was a good fit, too."

Soon after joining the firm, Maurone attended an intense, two-week training session at USLI, a carrier the agency represents. "It was a crash course on everything from product to team building to presentation skills," he says. "They ran us ragged." After that immersion, he tagged along with Dalton on some appointments, asked lots of questions, listened and took notes.

According to Maurone, years of business experience buying and selling products made him comfortable from the start. "For example, if I get the sense from someone that I can sit on the same side of the table with them or 90 degrees from them, as opposed to directly across the table, I will," he explains.

"I try to put myself in the buyer's shoes," he adds. "As a business person who signed payroll checks and insurance checks, I think I know what someone is thinking. It could be anything from, 'Oh, the insurance guy is here again; we really need to button this up' to 'I see your point on that coverage.'"

Maurone's experience, coupled with a passion for analysis, helps in other ways, too. "Agents ask for copies of policies to see if they can broaden coverage or lower costs," he explains. "That may be the first time anyone actually read the policy. Most insureds don't. When I bought insurance policies, I did read them. That's who I am, and it helps as I deal with prospects and clients.

"I want my customers to think of me as a partner," he adds. "If they succeed, I succeed. I know that's a cliché, but clichés exist because they serve a purpose."

A large part of Maurone's work over the past year has been building relationships in certain markets. "As a former telecommunication contractor and as a current member of different nonprofit boards, I understand how people think in certain circumstances," he explains. "I know first-hand what their concerns are."

As confident as he is in sales situations and business meetings, Maurone recognizes his limitations. "If someone asks me about something I have no experience in, I'll tell them straight out, 'I don't know enough about that to have an intelligent conversation, so I'll have none, but I'll research it and come back to you with a competent answer,'" he says. "Once I have my hands and head around it, I'll get involved. But I believe I'll say 'no' more than most people."

According to Dalton, the decision to bring Maurone on is working out well. "I've given him and Dave Angelo, our other producer, blueprints and goals," he explains. "We have sales meetings and they are accountable, but I don't speak to them as if they don't know anything about sales, because they do.

"Bobby is out building relationships," he adds. "He's taking a deliberative approach. We just went through his fourth quarter numbers, and he has a lot in his pipeline. It's all coming together quite nicely."

According to the Big "I" definition of young agents—those under 40 years of age or with less than five years of experience in the industry—Maurone may well be the oldest young agent around. He chuckles at that thought, saying, "I don't know about that, but I do know I'm one of the happiest."